Synlett 2023; 34(12): 1419-1424
DOI: 10.1055/a-2021-9599
cluster
Special Issue Honoring Masahiro Murakami’s Contributions to Science

Solid-State Silver-Catalyzed Ring-Opening Fluorination of Cyclobutanols by Using Mechanochemistry

Ryota Isshiki
a   Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
b   Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
,
Koji Kubota
a   Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
b   Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
,
Hajime Ito
a   Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
b   Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
› Institutsangaben
This work was financially supported by the Japan Society for the Promotion of Science (JSPS) via KAKENHI grants 22H00318, 21H01926, 22K18333, 22H05328, and 22K20523, by the JST via the CREST grant JPMJCR19R1, by the FOREST grant PJ2521A02I, and by the Institute for Chemical Reaction Design and Discovery (ICReDD), established by the World Premier International Research Initiative (WPI), MEXT, Japan.


Abstract

In this report, we demonstrate that a ball-milling technique facilitates fast and efficient silver-catalyzed ring-opening fluorination of cyclobutanols. This is the first report of a catalytic C–C bond-cleavage/functionalization reaction under solid-state mechanochemical conditions. The developed protocol affords a high yield of γ-fluorinated ketones within much shorter reaction times, and requires less silver catalyst and Selectfluor compared with the previous solution-based conditions. Notably, the process can be carried out in air. Because of the reduced use of chemicals and the simple time-saving experimental procedures, this technique is an efficient and environmentally friendly way to access γ-fluorinated ketones.

Supporting Information



Publikationsverlauf

Eingereicht: 18. November 2022

Angenommen nach Revision: 29. Januar 2023

Accepted Manuscript online:
29. Januar 2023

Artikel online veröffentlicht:
03. Mai 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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  • 15 4-Fluoro-1-phenylbutan-1-one (2a); Typical Procedure Cyclobutanol 1A (44.3 mg, 0.30 mmol, 1.0 equiv), AgF (1.9 mg, 0.015 mmol, 5.0 mol%), and Selectfluor (107.2 mg, 0.30 mmol, 1.0 equiv) were placed in a ball-milling vessel (ZrO2, 10 mL) loaded with one grinding ball (ZrO2; diameter: 10 mm). H2O (31 μL, 0.20 μL/mg) was added from a syringe. The vessel was then closed in air without purging with an inert gas, and placed in the ball mill (Retsch MM400) for 30 min at 15 Hz with heating by a heat gun to an internal temperature of 55 °C. After 30 min, H2O and Et2O were added and the mixture was extracted with Et2O (×3). The combined organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography [silica gel, hexane–EtOAc, 50:1] to give a colorless oil; yield: 33.8 mg (68%). 1H NMR (400 MHz, CDCl3): δ = 2.16 (d quint, J = 27.6, 6.4 Hz, 2 H), 3.16 (t, J = 6.4 Hz, 2 H), 4.57 (dt, J = 48.8, 6.4 Hz, 2 H), 7.48 (t, J = 8.0 Hz, 2 H), 7.58 (t, J = 8.0 Hz, 1 H), 7.99 (d, J = 8.0 Hz, 2 H). 13C NMR (101 MHz CDCl3): δ = 24.8 (d, J C–F = 20.2 Hz, CH2), 33.9 (d, J C–F = 4.8 Hz, CH2), 83.3 (d, J C–F = 165.9 Hz, CH2), 127.9 (CH), 128.6 (CH), 133.1 (CH), 136.7 (C), 199.0 (C). 19F NMR (376 MHz CDCl3): δ = –220.9 to –221.4 (m, 1 F). HRMS-EI: m/z [M]+ calcd for C10H11FO: 166.07939; found: 166.07934. The NMR spectra agreed with those reported in the literature.8h